Furazan derivatives have been of interest for the construction of rocket propellants and explosives ingredients because the compounds are relatively insensitive and yet provide favorable oxygen balance. The starting point is usually diaminofurazan, and oxidation converts amino groups to nitro groups, and also to azo and azoxy groups. The azo and azoxy groups serve as energetic linking groups that link two or more furazan rings: Solidyuk, G. D.; Boldyrev, M. D.; Gidaspov, B. V.; Nikolaev. V. D. Zhur.Org.Khim. 1981 17(4), 861-5. Kulagina, V. O.; Novikova, T. S.; Mel""nikova, T. M.; Khmelnitskii, L. I. Chem. Heterocyclic Comp. 1994, 30(5), 631-5. Kulagina, V. O.; Novikova, T. M.; Khmelnitskii, L. I. Chem.HeterocyclicComp. 1994, 30(5), 629-30. Sheremetev, A. B.; Kulgina, V. O.; Aleksandrova, N. S.; Dmitriev, D. E.; Strelenko, Y. A.; Lebedev, V. P.; Matyushin, Y. N. Propellants, Explosives, Pyrotechnics 1998, 23,142-9.
The use of reduction chemistry to modify the structures of furazans has been little studied. It has recently been reported that the reduction of 3,3xe2x80x2-diamino-4,4xe2x80x2-azoxyfurazan with zinc in acetic acid gave 3,3xe2x80x2-diamino-4,4xe2x80x2hydrazofurazan, which could be oxidized to the desired 3,3xe2x80x2-diamino-4,4xe2x80x2-azofurazan with air. Chavez, D.; Hill, L.; Hiskey, M.; Kinkead,S. J. of Energetic Materials, Vol.18, p. 219-236(2000). Selective reductions of azoxy groups in the presence of nitro groups are not trivial. Thus, March J., xe2x80x9cAdvanced Organic Chemistryxe2x80x9d, McGraw-Hill Book Co., New York, N.Y., 1977, p. 1125-1132 reported that nitro groups and azoxy groups are both reduced by zinc/acid.
This invention relates to the novel compound 3,3-Dinitro-4,4xe2x80x2-hydrazofurazan and the methods of preparation.
One method of preparing 3,3-Dinitro-4,4xe2x80x2-hydrazofurazan comprises partially reducing 3,3xe2x80x2-Dinitro-4,4xe2x80x2-azoxyfurazan.
Another method of preparing 3,3xe2x80x2-Dinitro-4,4xe2x80x2-hydrazofurazan according to this invention is by the partial reduction of 3,3xe2x80x2-Dinitro-4,4xe2x80x2-azofurazan.
3,3xe2x80x2-Dinitro-4,4xe2x80x2-hydrazofurazan is valuable as an ingredient for rocket propellants and explosives because of its combination of high oxygen balance, high melting point, and low sensitivity to impact and friction.